Bis-(2-chloro-ethyl)-methyl-(8-nitro-naphthalen-1-ylmethyl)-ammonium

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Bis-(2-chloro-ethyl)-methyl-(8-nitro-naphthalen-1-ylmethyl)-ammonium
• 英文别名: Bis(2-chloroethyl)-methyl-[(8-nitronaphthalen-1-yl)methyl]azanium
• 化学式: C₁₆H₁₉Cl₂N₂O₂
• 分子量: 342.245
• InChiKey: VNXCXXXBZQXERY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N-bis(2-chloroethyl)-N-methyl-N-[(8-nitro-1-naphthyl)methyl]ammonium chloride 在 叔丁醇 作用下， 以 水 为溶剂， 生成 Bis-(2-chloro-ethyl)-methyl-(8-nitro-naphthalen-1-ylmethyl)-ammonium
  参考文献：
  名称：

  Pulse Radiolysis Studies on the Fragmentation of Arylmethyl Quaternary Nitrogen Mustards by One-Electron Reduction in Aqueous Solution

  摘要：

  The radical species formed on the reaction of e(aq)(-) with a series of aryl compounds, all containing a N,N-bis(2-chloroethyl)-N-methylammoniomethyl substituent, have been studied in neutral aqueous solutions by pulse radiolysis using optical absorption spectraphotometry. The benzene, 1, and 4-methylsulfonylbenzene, 2, derivatives fragmented Immediately to yield different amounts of benzyl radicals, but the 2-nitrobenzene, 3, and 4-nitrobenzene, 4, derivatives were reduced to long-lived radical anions which decayed by bimolecular processes. These nitrobenzene derivatives differed from the corresponding benzyl halides in that they did not fragment to benzyl radicals. Similarly, no evidence was found for the formation of a benzyl-type radical from the radical anion of the 8-nitronaphthalene derivative, 5. However, benzyl-type radicals were produced upon intramolecular electron transfer from the initially formed radical anions of the 4-nitro-5-imidazole, 6, and the 5-nitro-2-pyrrole, 7, derivatives at rate constants of (8.0 +/- 1.0) x 10(3) and (1.0 +/- 0.1) x 10(4) s(-1) respectively; The latter heterocyclic analogues provide an approach for release of cytotoxic tertiary amines via enzymatic or radiolytic reduction in hypoxic regions of tumors.

  DOI：

  10.1021/jp972311a

文献信息

• Pulse Radiolysis Studies on the Fragmentation of Arylmethyl Quaternary Nitrogen Mustards by One-Electron Reduction in Aqueous Solution
  作者：Robert F. Anderson、William A. Denny、Wenjie Li、John E. Packer、Moana Tercel、William R. Wilson

  DOI：10.1021/jp972311a

  日期：1997.12.1

  The radical species formed on the reaction of e(aq)(-) with a series of aryl compounds, all containing a N,N-bis(2-chloroethyl)-N-methylammoniomethyl substituent, have been studied in neutral aqueous solutions by pulse radiolysis using optical absorption spectraphotometry. The benzene, 1, and 4-methylsulfonylbenzene, 2, derivatives fragmented Immediately to yield different amounts of benzyl radicals, but the 2-nitrobenzene, 3, and 4-nitrobenzene, 4, derivatives were reduced to long-lived radical anions which decayed by bimolecular processes. These nitrobenzene derivatives differed from the corresponding benzyl halides in that they did not fragment to benzyl radicals. Similarly, no evidence was found for the formation of a benzyl-type radical from the radical anion of the 8-nitronaphthalene derivative, 5. However, benzyl-type radicals were produced upon intramolecular electron transfer from the initially formed radical anions of the 4-nitro-5-imidazole, 6, and the 5-nitro-2-pyrrole, 7, derivatives at rate constants of (8.0 +/- 1.0) x 10(3) and (1.0 +/- 0.1) x 10(4) s(-1) respectively; The latter heterocyclic analogues provide an approach for release of cytotoxic tertiary amines via enzymatic or radiolytic reduction in hypoxic regions of tumors.